Big Mac’s Adventures in Rarity’s Gemhole

by One Terrible Writer

Rating: mature
Tags: Comedy, Romance
Length: 4386

Big Mac and Rarity take their relationship to the next level. And by 'next level', I mean 'anal sex'.

One night, Rarity invites Big Mac round for a night he'll never forget. And by 'never forget' I mean 'anal sex'.

Is one pony enough for Rarity? Let's hope not, because Caramel and Doctor Whooves also drop round, fascinated by Rarity's ass! Can Rarity handle all the sexy fun?

And by 'sexy fun' I mean…

Published 1970-01-01 00:00:00 UTC
Last updated 2013-02-02 18:50:01 UTC

Chapter 1

“Oh, Big Mac, you are so…. Big!”

Big Mac did his best to stifle a beaming grin as he tumbled through the door to the Carousel Boutique, a giggling Rarity in tow. The night’s karaoke evening at the town hall had gone better than expected. Far, far better.

“Shh! Shh!” Rarity motioned to Big Mac with a swipe of her hoof, swaying groggily side to side as she violently slammed the door to shut out the crisp night air. “Sweetie Belle’s having a sleepover upstairs, we need to be quiet!” she hissed urgently as she staggered into a nearby trestle table stacked high with sewing equipment that clattered to the ground.

Big Mac simply sat down on the floor and wiped his brow. The sweats from the night’s exertions were beginning to show, and he was feeling rather woozy himself. “Ah don’t know what Applejack put in that apple cider!” he announced. He did, though. It was apples. Making conversation was always polite though.

After a quick flurry of activity where she somehow made the mess in the room worse, Rarity swept her mane back to regain some composure, and with one smooth motion, slid across the floor to nuzzle her head against Big Mac’s side.

“Mmm, I can’t believe you won the karaoke, Big Mac, I wouldn’t have you down for somepony who knows all the words to ‘Modern Major-General’. It makes little me wonder what else you’re really good at.” She twisted her head slightly to nip at Big Mac’s neck.

Big Mac smiled again. “Ee-yup.” It had been a good night. There were many ponies in Ponyville whom Big Mac had kept his eyes on. He had dated Cheerilee on and off, though it hadn’t really led anywhere. He admired Fluttershy for her kind nature, and Rainbow Dash for her adventurous personality. He had held a torch for Pinkie Pie for a long time, though one night with her and an icing sugar overdose soon extinguished that flame. Roseluck, Sassaflash, even Derpy, he’d felt attracted to them all. But not Rarity. From the first time he set eyes on her, he knew that beautiful, perfect mare was forever out of his reach. She was just in another class.

And yet, here she was offering herself up on a plate. It was funny what a night of karaoke, hard apple cider, and and defeating the dark god 'Fn'Ar'Grah' in a singing contest could do.

“You know…” Rarity fluttered her long eyelashes up at Big Mac. “I’ve always found you very –” She cut her own words off as she lunged towards Big Mac’s mouth, clamping her lips around his, her tongue snaking into his mouth.

Big Mac’s eyes went wide as Rarity cut off his oxygen, but he didn’t care. Heart pounding nineteen to the dozen at the beautiful pony melting in his hooves, he kissed her back deeply, pressing his warm throbbing body to her, stroking a hoof over her sides and enjoying every subtle curve.

“I want you, Big Mac!” Rarity pulled away from the kiss dramatically, her sapphire blue eyes gazing deeply into his. “I wanted you since the moment I met you, and besides…” She gave a coy smile. “You saved my life at the karaoke bar. If you hadn’t out-danced those Devil Monks that gate-crashed the party, I don’t know what would have happened!” She leaned forwards to whisper in her ear, one hoof idly trailing over her stomach. “They could have done anything to me.” She bit the end of his ear softly. “And I guess that means now you get to.”

Attempting to keep his composure, Big Mac swallowed, feeling his member beginning to stiffen uncontrollably as Rarity made her move. This was all he’d ever wanted, all he’d ever dreamed of, and it was happening right here, right now, on the floor of Rarity’s boutique.

“There’s just two things you need to know,” Rarity purred as she took control, gently pushing Big Mac over to roll him onto his back. His cock stuck up in the air, twitching helplessly before the white pony. “Firstly,” Rarity continued, “I am a lady. You know what that means?”

Big Mac stared at Rarity in confusion, his exposed  cock swelling to its full length as it swayed in front of Rarity. “Uh….” he paused. “I-it means you want to wait for marriage?”

“No!” Rarity rolled her eyes and then leaned forwards, her delicate pink tongue darting towards the base of Big Mac’s rapidly rising cock, lapping up the full length of his shaft in one stroke, finishing on the tip where she finished off with a kiss. “I am a lady, Big Mac. This means I do not spit. I swallow.”

Big Mac wanted to cry out, the blood roaring into his cock from Rarity’s touch, throbbing and aching for the perfect pony that stood before him. He mustered up all the self-control that he had to avoid finishing there and then. That would be embarrassing. “T-that won’t be a problem!” he choked out.

“Good.” Rarity nestled herself in between his legs and gently stroked Big Mac’s shaft against her cheek. “Of course, if you did feel the need to cum over me, that would not be a problem. I need to keep my coat its brilliant shade of white.” She fluttered her large eyes innocently at Big Mac before leaning forwards to lap at the head of his cock again. “My natural shade is actually pink.”

Biting hard on his lip, Big Mac whimpered before Rarity, consumed by desire. His cock started to leak pre-cum, and it was all he could do to not blast a load in her face there and then. “A-ah want you, Rarity. Ah want you so bad!”

Rarity stroked a hoof appreciatively up the length of his cock, smearing his pre-cum over her hooves. “I can see why they call you Big Mac,” she purred.

“M-my parents gave me that name!” Big Mac grunted.

Rarity frowned. “Yes, I know, I was referring to…” She shook her head. “Never mind, moment’s gone.” With one last lap around the tip of Big Mac’s cock, she darted away with a giggle, positioning herself over a nearby workbench, her flank wiggling enticingly in the red stallion’s direction. “Come get me, Big Mac! I want you inside me so badly!”

Big Mac could barely walk, such was the throbbing in his cock, but he staggered back to his feet, his huge member swinging wildly from side to side as he approached that delicious rear, eyes fixed on its perfect round shape and the purple tail that swung invitingly from side to side.

“Ee-yup!” Big Mac eagerly reared up, positioning himself over Rarity, his hooves at her side, his belly pressing against her back and savouring the heat that emanated from her small frame. His cock felt like it was about to explode as he rubbed it across her pussy lips, the anticipation of burying himself in her tight folds too much to contemplate. He sharply drew in a breath, preparing to thrust his way to victory, when –

“Stop! Right there!” Rarity waved a hoof at Big Mac, craning her head around with an annoyed expression on her face. Big Mac froze like the proverbial rabbit in front of a cart. “Big Mac, the second thing you should know is that I am a virgin.”

“Oh. Oh! Ah…” Big Mac looked at his mighty cock about to plough into Rarity’s delicate body. “Ah’ll be gentle.”

“No, you misunderstand.” Rarity shook her head. “I am a virgin, and as such, you may not stick it in there. When I have sex, it is in my ass, to maintain my innocence and purity.” She wiggled her behind at Big Mac again, to make the point. “I trust that is not a problem.”

Big Mac stared at the ass that loomed into view. Perfectly rounded, plump yet firm, and with a tiny little entrance that just screamed out for his cock. He placed his forehooves firmly on Rarity’s cutie marks for added grip, and lined his member up against her. It was all he could do to not drive instantly in. “Ain’t no problem, ma’am!” he replied gratefully.

Rarity gave a sultry smile as she winked at Big Mac, and then stretched out her hooves in front of her, staring ahead as she flung her head back, and arched her back, to press her rump hard against Big Mac’s throbbing member. “Take me, Big Mac! Take me now!”

Sweat pricked on Big Mac’s brow as he gripped Rarity firmer, starting to press himself into her asshole. He bit his tongue, grunting from the effort as he tried to press his huge member into Rarity’s firm behind. “Ah don’t wanna hurt you,” he called down in concern.

“Hurt me!” Rarity pressed her ass back against Big Mac, the heat from her entranceway sending him slightly crazy. “I want you in me Big Mac, I want you to stuff me ‘til I scream!”

Big Mac glanced at the nearby stairwell, thinking of Sweetie Belle’s sleepover going on upstairs, but then shrugged. Maybe Rarity wouldn’t scream that loudly. “Ee-yup!” he announced, nodding his assent as he grabbed Rarity’s ass, spreading the cheeks apart as far as he could while pressing the huge head of his cock into the trembling pony.

He threw his head back, bellowing out as he penetrated Rarity, her tight hole like a vice on his cock as he pressed further into her depths. Before him, Rarity lay sprawled over the table, whimpering, pounding the hard wooden surface with one hoof as inch by inch, Big Mac’s girth stretched her tight ass.

“O-oh Celestia, more!” Rarity’s face flushed bright red (or was that her natural colouration coming out, Big Mac wondered), squirming helplessly before him as her body throbbed with the invasion of Big Mac. It was barely in, but already she felt like she was being ripped in half. “D-deeper, Big Mac, I demand it!”

Big Mac was only too happy to oblige. Holding Rarity firmly, he pressed his haunches into her, not caring about the need for quiet as he cried out, his voice mingling with Rarity’s moans of passion. He sunk himself further, watching with fascination as his cock burrowed into Rarity’s ass at a slow but steady pace, savouring every squeeze and twinge of her body.

Rarity let out a whimpering cry as Big Mac almost went hilt-deep, her pure white body speared ass-first on the massive stallion’s cock. Her eyes bulged from the mixture of pleasure and pain as the gigantic organ filled up her ass, but she did her best to keep her dignity. “Mm, oh yes, now fuck me, Big Mac, fuck me hard like a mule!”

The phrasing was a bit strange, but Big Mac wasn’t in a position to decline. He started to slowly pull out of Rarity, being careful not to go too fast at first, and after a few inches, pushed back in again to be greeted with a loud, low moan from his lover. The feeling as he pumped into her was incredible, and he started to move faster and faster, making longer thrusts into that delicate body.

Rarity was a mess as Big Mac pounded into her, flicking her head from side to side, grinding her ass back against him as she was filled. “Oh yes,” she warbled, lost in her own lust. “Fuck me, Big Mac! Fuck my ass! Fuck me like a lady, good and hard!”

With a wide grin, Big Mac started to ram her harder and harder, the sight of his huge cock delving into that tight hole making him impossibly harder. He placed one hoof on her back as he thrust away, staring at the simpering mare who was taking him like a pro, and then casually up at the ceiling, delighting in the experience and sensation. This was the best day of his life, he thought, his cock reaming that tight ass. He pulled further out and then deeper in, causing Rarity to moan harder. Out, then in. Out, then in.

Out.

Big Mac thrust in, but something was wrong. His cock bounced off the entrance to Rarity’s ass. The incredible sensation of tightness was still there though. He pushed again. Nothing happened. He glanced back down in confusion, and his jaw dropped open, stifling a gasp. Something had gone horribly wrong.

His cock was still in Rarity’s ass. But Rarity’s ass wasn’t in Rarity’s ass.

What looked like a pink and purple sock was stretched out from Rarity’s asshole, squeezing tightly round Big Mac’s cock like a stocking. Big Mac stared in horror, dumbstruck at the sight. Rarity has been so tight, his member so huge, that he had pulled it out in his passion, and now it clung tightly to his cock.

“What are you doing? Keep going, mmm!” Rarity shuffled in front of the panicked stallion impatiently, about to turn around.

“No, no, don’t worry, it’s ah… a pause is sexy!” Big Mac suddenly blurted out. “Anticipation, keep lookin’ ahead!” Desperately he tried to force his cock back into her, but the prolapsed colon that clung to his cock just wouldn’t fit back in! Sweat started to pour down his forehead, not in lust this time, but sheer alarm.

“Mmm yeah, rub it against my asshole, big boy!” Rarity groaned as Big Mac frantically tried and failed to stuff Rarity’s insides back into her. “Destroy my ass!”

“Y-yes ma’am!” Big Mac squirmed as he attempted wiggling his cock back into Rarity. The colon and opening seemed to be inflamed though.  It just wasn’t happening, and the constricting sensation of the colon around his cock kept it big and hard.

Casting his eyes about frantically for something, anything that could help him get out of this tricky situation,  he suddenly saw a familiar orange stallion trotting by the outside window. “Caramel!” he hissed through clenched teeth, in the hope that Rarity wouldn’t hear. “Caramel!”

“What’s that dear? Cum? Oh yes, cum in me!” Rarity rocked her hips against Big Mac, causing the stallion to shudder.

“A-ahm just goin’ to take a run-up!” Big Mac announced. “Ya’ll just stay there, Rarity, it’s sexier like that.” Turning frantically before Carmel went out of earshot, he hissed again “Caramel!” It was no good. Holding onto Rarity’s behind, Big Mac slowly tried to slip his cock out of its tight sleeve. Rarity’s gut strained and stretched as it refused to let go, and then suddenly with a wet slurping sound, Big Mac tumbled backwards.

He wasn’t free though. The colon was still tightly around his cock, but now it had seemingly ripped free from Rarity’s asshole. A trail of her guts hung out of her asshole, connecting her body to Big Mac’s cock. Gathering his thoughts, Big Mac slowly tried to edge towards the window, wincing at every tug on his cock the colon made as it unspooled from Rarity.

“Oooh, I like what you’re doing, are you trying something new?” Rarity purred.

“Y-yeah, kinda. Just stay there!” Big Mac finally made it to the window, craning his head out as he half-yelled: “Caramel! Get over here!”

Caramel turned his head, and galloped quickly over to Big Mac, peering through the window. “Hey Big Mac, I heard you got lucky with Rarity, and… whoa!” His eyes boggled as he saw the long red sausage-shaped object trailing from Big Mac’s crotch to Rarity’s behind. “Wow, holy Celestia! I knew they called you Big Mac but I didn’t realise it was that big! That’s like, ten metres long!”

“What? No! Caramel, no! Ah have a problem!” Big Mac leaned through the window pane, desperate to not let Rarity hear. “Ah fucked Rarity so hard in the ass her ass broke an’ it got stuck on mah cock!”

Caramel’s face paled as he reassessed the situation. “Oh. Well, yes, that is a problem. Put it back in!”

“Ah tried! It won’t go!” Big Mac wiped another bead of sweat from his damp mane. “Ah need some help, an’ you’re a good friend!”

“Okay, okay.” Caramel rubbed his chin. “What about this. I cover myself with flour so I’m white like Rarity, draw some diamonds on my flank, and then you can stuff your cock in my ass. Mine isn’t broken!”

Big Mac blinked. “What?”

Caramel pursed his lips. “Oh, sorry, I completely misunderstood your problem. You want to try to fix Rarity. Got it. Be right round!” With that, he vanished from view.

Big Mac gingerly made his way back to Rarity, reeling in the expended colon as he did so. “Ah… ah’m going to bring Caramel in to ah… be extra sexy!” he announced.

“Mmm, a threesome, delightful!” Rarity started to turn round again, but Big Mac leapt forwards and blocked her view.

“Ah… ah think you should keep lookin’ away, so you don’t see what we’ve got planned. Anticipation an’ the like!” Big Mac stared at the spool of guts that now sat on the floor, one end attached to Rarity, the other to his throbbing cock. “Ah don’t want to ruin the surprise.”

“I feel all light!” Rarity trilled. “Super, simply marvellous idea darling.”

“Hi, Big Mac!” Caramel slipped in through the door, a fixed grin on his face, attempting to keep a cool disposition. “Hi Rar – oh by Celestia’s beard, Rarity’s ass!” He stared at the scene as the full horror of the situation grabbed him by the throat.

“Yes, it is rather amazing, isn’t it!” Rarity simpered.

Caramel crept up to Rarity’s ass and studied the damage. “Y-yes, it is!” he squeaked, turning to Big Mac to mouth a frantic but silent ‘What do we do?’

Big Mac threw his hooves up in despair, but then an idea struck him. “H-hey Rarity, we’re just gonna put a curtain between us so you can’t see what sexy things we’re doing!” He motioned desperately to Caramel. “Go on, do it!”

Caramel leaned forwards and kissed Big Mac.

Big Mac pulled away in shock. “N-no, I mean the curtain, get the curtain!”

“Oh!” Caramel leapt into action, fetching a free-standing curtain that had been used in one of Rarity’s fashion shows and wheeling it over to the table, placing the drapes across Rarity’s body so her view was blocked by the heavy fabric.

“I just know you’re going to be up so to something naughty back there!” Rarity purred to Caramel before her face became stern. “Just make sure you don’t get up to anything gay with Big Mac. This is all about my ass, got it?”

“Ha. Ha. Ha. Yes.” Beads of sweat rolled down Caramel’s face as he nipped round the other side. “What the hay do we do?” he whispered to his co-conspirator.

“Ah don’t know! Ah thought you’d know!” Big Mac glanced at the curtain in case Rarity heard anything, but it seemed that for the moment, the heavy material blocked any immediate sounds. Besides, she had started to moan to herself, which only made him harder still. “You stretch her ass, ah’ll try to stick it back in!”

Cautiously, Caramel pulled Rarity’s ass-cheeks apart, wincing at the sight. Big Mac grunted and groaned as he did his best to push the heap of colon back in, but it would just not go past the inflamed asshole.

“This is a nightmare!” Caramel moaned flopping to the floor. He brightened suddenly. “Or is it? I’ve got an idea!” With that, Caramel darted from the room, leaving a shaken Big Mac alone with Rarity.

“I hope you boys have got something wicked planned!” Rarity wriggled her ass, causing a bit more colon to slip out onto the pile already on the floor. “I really want you guys to bottom me out!”

Big Mac was saved from having to reply as a triumphant Caramel crashed through the door, a familiar-looking chestnut stallion in tow. “Rarity, you don’t mind if Doctor Whooves joins in, do you?” he called out.

“Mmm, a foursome? Delightful!” Rarity simpered.

Doctor Whooves rolled his eyes. “I don’t see what all the fuss is about, but thanks for rescuing me, Caramel. I need to stop getting seduced by Twilight Sparkle. She’s insufferable! ‘Cum on my wings,’ she keeps ordering. ‘Fuck me like a princess’.” He leant towards Big Mac in a conspiratorial whisper. “They’re not even wings, they’re just paper plates she’s taped to her sides, it’s pathet – oh my Celestia, look at Rarity’s ass!”

“Oh, I know, isn’t it simply divine!” Rarity purred from behind the curtain.

“You’ve gotta help me!” Big Mac pointed at his colon-covered cock in frustration. “Ah fucked her too hard an’ it broke her ass, an’ now it’s all come out.”

Doctor Whooves rubbed his chin for a moment. “Okay I’ve got this. I cover myself with flour so I’m white like Rarity, draw some diamonds on my flank, and then you can stuff your cock in my ass!”

An awkward silence reigned in the room for a moment. Caramel eventually spoke up. “No, no, he wants to fix Rarity’s.”

“Ah yes, I see…” Doctor Whooves trotted over to examine Rarity’s behind, and to the consternation of his two friends, wrapped his hooves around the colon and gave it an experimental tug. Rarity moaned from behind the curtain in the throes of passion. “So it’s ah, stuck on your cock, yes?” he whispered, raising an eyebrow at the red mass tightly wrapped around Big Mac’s member.

“Ee-yup!” Big Mac gulped. “It won’t come off! You’ve gotta help, Doc!”

“Don’t worry, I know what to do!” Doctor Whooves turned back to Rarity and started to yank on her colon harder, reeling more and more of it out.

“Oh yes, harder, harder!” called Rarity from behind the curtain. “I don’t know what you boys are doing, but keep doing it!”

“What the hay are you doing!” Caramel hissed in panic. “You’re supposed to be putting it back in!”

“I am!” Doctor Whooves kept on tugging, a larger pile of guts now by his hindquarters. “I’m going to pull it all out this way so I can… Uh… You know, stuff it back in the other end!”

“Her mouth?” Big Mac raised a hoof as if to punch Whooves. “How in tarnation is that going to work!?”

“I don’t know, I’m not a real doctor!” Doctor Whooves held up a large red circular object which plopped from Rarity’s ass. “Now what the hay do you think this is?” He shrugged, and threw it to the side. “Eh, I’m sure it’s not important.”

Caramel bit his lip, looking at the mess Whooves was making, and then at Big Mac’s still inflamed member. “We still need to get this off him!” he announced, casting his eyes about for something sharp. “Maybe if we can cut it off, or use some salve…” His hoof brushed against Big Mac’s colon-covered cock. At Caramel’s touch, Big Mac’s cock instantly deflated.

“Oh,” said Caramel dejectedly, his hopes and dreams for a loving future with the big red stallion dashed into oblivion. “I see how it is.”

“I think I’ve got it all!” Doctor Whooves triumphantly announced, as he continued to reel out Rarity’s internal digestive tract. “Hang on, hang on!” He gave a sharp tug, and something large and wet plopped out. “Hmm, is that a kidney or a liver, do you think? Again, not a real doctor; not got a clue.”

Big Mac stared at the pile of organs at his hooves. “Ah… what… why did you do that?”

“Mmm boys, what are you doing back there, I hope you’ve got a wonderful surprise! I feel so empty without cocks in me!” Rarity’s voice cooed from the other side of the curtain. Three heads turned towards it in horror.

“What? I fixed the problem, didn’t I?” Doctor Whooves shook his head in annoyance. “There’s nothing hanging out of Rarity’s ass, Big Mac’s cock is now free to do whatever Big Mac’s cock is free to do, what’s the problem?”

Big Mac pointed at the pile of innards by their hooves. “That’s the problem!”

“It’s not a problem, we just need to hide it somewhere and sew up the hole! She’ll never notice, trust me, mares never notice important stuff!” Doctor Whooves started to look around. “There must be a sewing kit around here somewhere, it’s a dress shop! One of you sew it up and we’re home and dry!”

“I’m not doing it!” Caramel flicked his mane in disgust at the idea. “I can’t believe you did that, Whooves! You do it!”

“I can’t sew her up!” Whooves protested. “That’ll be practising medicine without a license, I’d go to jail! One of you do it!”

“Will you just stop arguing!” Big Mac hissed urgently. “Rarity’s only got a curtain to stop her from hearin’ you yappin’ about her ass, and Sweetie Belle’s upstairs having a sleepover!”

“Right. Right. I see.” Whooves nodded, and then before anyone could stop him, he ran over to the stairwell. “Hey, girls, who wants to get their surgery cutie marks?”

A sudden thunder of hooves pounded down the stairs with an blood-chilling cry of “Cutie Mark Crusader Surgeons, yay!”

***

Rarity smelled the flowers on the windowsill, and sighed contently as she looked out at the beautiful picturesque village of Ponyville. The day was going wonderfully already – that morning in the bathroom, she had weighed herself and to her utter delight discovered she had lost over 20 pounds! It just showed what a regime of healthy eating and fitness could do for you.

She drifted back to her amazing evening with Big Mac the night before. She had unfortunately dozed off towards the end after Doctor Whooves had accidently dropped a large vase on her head repeatedly, and she had some rather odd dreams afterwards. Sweetie Belle shouting something about “sewing Scootaloo inside.” Still, dreams were funny things. She was still Ponyville’s most eligible pony.

She frowned, a strange itch on her behind. She turned to scratch it, finding only a perfectly smooth, flawless white rump. It felt like there was something missing, but she couldn’t put her hoof on it.

Rarity shrugged. It probably wasn’t important.

And that is why Rarity doesn’t have a bum.